Direct Observation of a Cationic Gold(I)–Bicyclo[3.2.0]hept‐1(7)‐ene Complex Generated in the Cycloisomerization of a 7‐Phenyl‐1,6‐enyne | Zendy

Brooner Rachel E. M. | Zendy; Brown Timothy J. | Zendy; Widenhoefer Ross A. | Zendy

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Direct Observation of a Cationic Gold(I)–Bicyclo[3.2.0]hept‐1(7)‐ene Complex Generated in the Cycloisomerization of a 7‐Phenyl‐1,6‐enyne

Author(s) -

Brooner Rachel E. M.,

Brown Timothy J.,

Widenhoefer Ross A.

Publication year - 2013

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201301640

Subject(s) - cycloisomerization , enyne , ene reaction , cationic polymerization , bicyclic molecule , chemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis

The reaction of enyne 1 with a 1:1 mixture of [LAuCl] and AgSbF 6 in CD 2 Cl 2 at −20 °C gave the gold complex 2 in 97 % yield (NMR spectroscopy). Warming a solution of 2 at 25 °C led to 1,3‐H migration ( t 1/2 ≈16 min) to form the gold complex 3 with 96 % selectivity. 13 C NMR analysis of 2 and 3 showed predominant metallacyclopropane character of the goldbicyclo[3.2.0]heptene bond.

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